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"My idea of heaven still is to drive the gravel farm roads of Umbria and Tuscany, very pleasantly lost - Frances Mayes


Guest limits

8 / 7

Days / Nights


Starting Rate Per Person
(Minimum 4)

Indulge in the ultimate Tuscan adventure on this Private Departure exploring the vineyards  and villages around medieval Cortona. Discover local culinary traditions, savor the region's distinctive wines, engage in a truffle hunt, and experience the iconic architecture of Siena and the beauty of Lake Trasimeno. This carefully curated itinerary combines the best of gastronomic delights, scenic landscapes, and cultural and historic exploration, promising an unforgettable journey in the heart of Tuscany. 


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    Land in Florence or Perugia airport and transfer to accommodations in Cortona

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    Lunchtime cooking class and walking tour of the medieval hilltown of Cortona

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    Wine estate tour and tasting followed by visit to picturesque Pienza

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    DAY 4. Etruscan Hills

    Exploration of Tuscan hidden gems including special dinner at Michelin-starred restaurant

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    DAY 5. Siena

    Wine estate visit and light lunch followed by guided tour of historic Siena and dinner on terrace of a private place

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    Boat ride on beautiful Lake Trasimeno including stop on the island of Isola Maggiore; Lunch and free time in the charming town of Castiglione sul Lago

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    Morning agriturismo visit including truffle hunt and lunch; evening farewell dinner

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    Transfer to Florence or Perugia airport for return flights


Fonte al Vento Villa

Nestled among olive groves and vineyards, this boutique accommodation provides a charming retreat in the picturesque Tuscan countryside. Just a short walk from the town of Cortona, the villa offers an authentic Italian experience, offering traditional architecture, elegant interiors, and postcard views of the surrounding area. The property features two outdoor pools, restaurant, bar, garden and terrace, and complimentary Wifi. Rooms are equipped with air conditioning, tea/coffee making facilities, and bathrooms containing toiletries and hair dryer. While staying at the villa, guests also have access to a lounge area, fully-equipped kitchen, and washing machine.

"In Tuscany, the landscape is a masterpiece painted by nature's brush, and its vineyards produce wines that are poetry in a bottle." - Ernest Hemingway

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  • Accommodations during program dates, including all taxes and fees
  • All activities and private excursions described in the itinerary along with services of local guides, entrance fees, and private transportation
  • Meals as detailed in your itinerary, including pre-arranged drink pairings
  • Private airport transfers with porterage on the first and last scheduled days of the program

Not Included

  • Airfare to/from arrival and departure cities
  • Travel insurance
  • Additional alcoholic beverages beyond what has been arranged by Experi to pair with the included major meals
  • Gratuities for drivers, local guides, porters, and included meals

Travel Insurance

Learn more about travel insurance and how it can help you prepare for the unexpected at

Travel Terms & Conditions

View our complete terms and conditions here at

Reservation process

Step 1:

Complete the form above indicating:

  • the number of travelers in your group
  • your preferred travel dates
  • the best way to reach you

Step 2:

We will contact you to discuss your preferences.

Step 3:

Based on our conversation, we will check availability, confirm pricing, and provide you with a detailed proposal.

Step 4:

To confirm the services and accommodations for your private departure, a non-refundable 50% deposit of the total trip fee is required.

Frequently Asked Questions (FAQs)

How a Private Departure Works:

What is the difference between a Private Departure and a Custom Program?

A Private Departure is a program that our destination specialists have meticulously crafted and curated to highlight the best of a particular destination. While we offer a few options to personalize your journey, the main framework of a Private Departure itinerary has been set. If you are seeking to make changes in the schedule or activities, a Custom Program may better suit your needs.

What is the process for reserving a Private Departure?

The first step is to complete the website form indicating the number of travelers in your group, your preferred travel dates, and the best way to reach you. Next we will connect with you to discuss your preferences. With these in mind, we will check availability, confirm pricing, and provide you with a detailed proposal. When you are ready to confirm arrangements, the final step is payment of a 30% non-refundable deposit. [Note: The deposit percentage amount may vary depending on the program.]

How far in advance should I plan?

The earlier you begin planning, the more flexibility you will have on dates and availability of accommodations and experiences, particularly if you are seeking to travel during peak times. We recommend contacting us as far in advance as possible before your desired departure date. While we can assist with last-minute travel planning, availability may be limited.

When is final payment due? What is the cancellation policy?

Final payment is typically due 90 days prior to departure although this time frame may vary depending on the specific program. In general, trips canceled more than 90 days before departure incur a Cancellation Fee of the deposit amount. Trips canceled 90 days or less before departure incur a Cancellation Fee of the full program price. (For full details, see our Terms and Conditions at: We highly recommend travel insurance to safeguard against unexpected circumstances such as family/medical emergency.

Do I need travel insurance?

We highly recommend travel insurance to protect your investment in your trip and help safeguard against unforeseen personal events. A range of coverages are available. Please note that certain coverages (such as "Cancel For Any Reason" coverage, which offers the most flexibility) must be purchased within a short window of time following your initial reservation deposit. We do not sell travel insurance, but if you are looking for more information, visit our website at:

Destination-Specific Information - Tuscany:

Who is this trip suitable for?

This trip appeals to food and wine enthusiasts seeking to become immersed in all the storied region of Tuscany has to offer including culinary traditions, exceptional wines, colorful history, and picturesque landscapes.

When is the best time of year to travel to this destination?

We recommend traveling to Tuscany in Spring or Fall when temperatures are generally pleasant but crowds are less dense. The fall grape harvest, the timing of which varies year to year, can be an interesting and fun time to visit, although the dates are difficult to predict.

What does the trip rate include?

Your trip rate covers accommodations, airport transfers, private transportation for all day trips and excursions, guided tours with knowledgeable local guides, exclusive access and activities, concierge services, and meals as detailed in your itinerary. The trip rate does not include airfare.


P.O. Box 10576
Bainbridge Island, WA 

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